This invention relates to novel 1-dimethyl-carbamoyl-3-substituted-5-substituted-1H-1,2,4triazoles which are useful as insecticides, compositions containing those compounds and methods of use.
Certain 1,2,4-triazoles have been disclosed as having pesticidal activity.
U.S. Pat. No. 3,308,131 describes a group of 1,2,4-triazoles having the general formula ##STR2## where X is oxygen or sulfur, R.sup.1 and R.sup.2 are aliphatic groups containing up to 14 carbons and which may be joined to form a heterocyclic ring with the carbamoyl nitrogen atom and R.sup.3 and R.sup.4, which together contain up to 14 carbon atoms, are free from aliphatic unsaturation and are selected from hydrogen, halogen, sulfonyl, mercapto, cyano, hydrocarbyl, halohydrocarbyl, nitrohydrocarbyl, hydroxycarbyloxycarbonylhydrocarbyl, hydrocarbylsulfonyl, hydrocarbylmercapto, nitrohydrocarbylmercapto, halohydrocarbylmercapto, aminohydrocarbylmercapto and hydrocarbyloxyhydrocarbyl. These compounds are disclosed to be useful as insecticides, in dyeing textiles and as analgesics.
U.S. Pat. No. 4,291,043 discloses 1-N,N-dimethylcarbamoyl-3(5)-alkyl-5(3)-alkylthioalkylthio-1,2,4-triazoles having insecticidal activity. The 3(5) substituents include i-propyl, s-butyl, t-butyl or optionally methyl-substituted cyclopropyl and a group having the formula EQU --S--CH(R')--(CH.sub.2).sub.n --S--R"
where R' is H or methyl, R" is lower (C.sub.1 -C.sub.4)alkyl and n is zero or one.
U.S. Pat. Nos. 3,973,028 and 4,038,387 disclose 1-dimethylcarbamoyl-3-branched alkyl-1,2,4-triazole-5-yl-(N-substituted)sulfonamides having insecticidal activity. The branched alkyl groups include C.sub.3 to C.sub.4 secondary or tertiary alkyl and cycloalkyl.
U.S. Pat. No. 4,054,664 discloses 1(2)-(N,N-disubstituted carbamoyl)-3,5-substituted-1,2,4-triazoles having insecticidal activity. The 3(5) substituents include isopropyl, s-butyl, t-butyl and S-R where R is methyl, ethyl, propyl, vinyl, prop-2-ynyl, but-2-enyl or 2-haloalkyl.
U.S. Pat. No. 4,255,435 discloses 1(2)-N,N-disubstituted carbamoyl)-3,5-substituted-1,2,4triazoles having activity against a variety of economically important insects and nematodes. The 3(5) substituents include i-propyl, s-butyl, t-butyl. The 5(3) substituents include SR where R is methyl, ethyl, propyl, vinyl, 2-propynyl, 2-butenyl and 2-haloallyl.
U.S. Pat. No. 4,160,839 discloses 1-N,N-dimethylcarbamyl-3,5-substituted-1,2,4-triazoles having insecticidal activity. The 3-substituents include t-butyl, propyl, cyclopropyl, isopropyl or 1-methylpropyl. The 5-substituents include S-R where R is 2-propynyl, allyl, 2-bromoallyl, 2-chloroallyl, 2-methylallyl, 1-methylallyl or 2,3,3-trichloroallyl.
U.S. Pat. Nos. 4,220,790 and 4,066,774 disclose 1-N,N-dimethylcarbamoyl-3-tert-butyl-5-methylthio-1,2,4-triazole having insecticidal activity and a method of killing insects using said triazole.
DE 3031191A1 discloses 1-dimethylcarbamoyl-3(or 5)-benzylthio-5(or 3)-alkyl-1,2,4-triazoles having insecticidal activity. The 5(or 3) substituents include isopropyl, s-butyl, t-butyl, or optionally methyl substituted cyclopropyl.
DE 3021232 discloses 1-dimethylcarbamoyl-1,2,4triazoles having insecticidal activity. The 3(or 5) position is substituted with the group ##STR3## wherein R.sup.1 is (C.sub.1 -C.sub.4)alkyl, R.sup.2 is hydrogen or methyl and n is 0 or 1.
EP 0029407 discloses 1-N,N'-dimethylcarbamoyl-3,5-substituted-1,2,4-triazoles having insecticidal activity. The 3-substituents include i-propyl, s-butyl, t-butyl or cyclopropyl. The 5-substituents include S(CH.sub.2).sub.n OR.sub.2 where R.sub.2 is (C.sub.1 -C.sub.3)alkyl and n is 1 or 2.
The present invention relates to 1-dimethyl-carbamoyl-3-substituted-5-substituted-1H-1,2,4triazoles. These compounds are distinguished primarily by their novel 5-position substituents.
Compounds of the present invention are also distinguished by their insecticidal activity against sucking insects such as those of the order Homoptera and especially those of the family Aphididae. Accordingly, compounds of the present invention are particularly suitable for controlling plant-destructive insects in crops of cultivated plants and ornamentals, especially in crops of fruit and vegetables.
It is therefore an objective of the present invention to provide novel compounds, and compositions containing said compounds, which possess insecticidal activity. It is a further objective of this invention to provide methods for controlling insects using the novel compounds.